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EuropSlsches Patentamt
European Patent Office
Office europ6en des brevets
(11)
EP0 741 177 A2
(12)
EUROPEAN PATENT APPLICATION
(43) Date of publication:
06.11.1996 Bulletin 1996/45
(21) Application number: 96105289.1
(22) Date of filing: 02.04.1996
(84) Designated Contracting States:
BE DE FR GB IT LU NL SE
(30) Priority: 03.05.1995 US 433285
(71) Applicant: National Starch and Chemical
Investment
Holding Corporation
Wilmington, Delaware 19809 (US)
(51) IntCl. 6 : C09J 11/06
(72) Inventors:
• Sharak, Matthew L
Franklin Park, New Jersey 08823 (US)
• Paul, Charles W.
Madison, New Jersey 07940 (US)
(74) Representative: Hagemann, Heinrich, Dr.rer.nat,
Dipl.-Chem. et al
Patentanwdlte
Hagemann & Kehl
Postfach 86 03 29
81630 MOnchen (DE)
(54)
Sucrose Benzoate as a tackif ier for water sensitive or biodegradable hot melt adhesives
(57) Hot melt adhesive compositions are prepared
from a water sensitive or biodegradeable thermoplastic
adhesive polymer using sucrose benzoate as a tackif ier.
More particularly hot melt adhesive compositions are
prepared from 10 to 90% by weight of a biodegradable
or water sensitive thermoplastic polymer, 5 to 80% by
weight sucrose benzoate, 0 to 80% by weight plasticiz-
ing diluent, 0 to 50% by weight wax and 0 to 3% by
weight antioxidant.
CL
LU
EP0 741 177 A2
Description
Hot mett adhesives are used commercially for a wide variety of applications. The major advantage of hot melt adhe-
sive systems is the lack of a carrier fluid which eliminates the need for drying the adhesive film once it is applied to the
substrate. This elimination of the drying step overcomes hazards associated with solvent usage and also allows for
faster production line speeds and lower transportation costs. Depending on the desired use, the degree of tack of the
hot melt adhesive may be tailored over a wide range to produce adhesives varying from pressure sensitive to non-pres-
sure sensitive in character. Non-pressure sensitives are used, for example, in bookbinding, bag ending, case and car-
ton sealing. Pressure sensitive hot melts are used in many applications, and particularly in disposables such as diapers,
sanitary products and the like, where room temperature tack and long open time are often required.
Hot melt adhesives have historically been based on petroleum derived polymers such as polyethylene, ethylene-
vinyi acetate, styreneic block copolymers, and polypropylene to name a few. These compositions are further tackified,
plasticized and reinforced with a variety of resins, oils and waxes which are also derived from both petroleum and nat-
urally occurring feedstocks. These classic compositions suffer from the cyclical price cycles common to all oil derived
materials, and also are generally very resistant to degradation once the articles employing them are disposed of.
The recent growing movement away from petroleum derived raw materials to those derived from renewable, natural
resources has led to the use of new water sensitive, biodegradable and/or compostable polymers as the base polymers
in hot mett adhesive compositions. Thus, water sensitive and/or degradable adhesive compositions have been pro-
posed containing such raw materials as hydroxybutyrate/hydroxy-valerate polymers, polytactide homo- or copolymers,
hydroxypropyl cellulose, cellulose acetate, starch acetate, hydroxy functional polyesters and the tike. While the resultant
adhesives may be improved with respect to their water sensitivity and/or degradability, the overall water sensitivity
and/or degradability of the adhesive has been retarded by the presence of other additives, such as tackif iers and plas-
ticizers conventionally used in adhesive compositions. In particular, due to the polar nature of the water sensitive or bio-
degradable polymer, finding a compatible tackif ier, but also degradable has been difficult.
There is thus a need for a tackifying material which will not only be degradable in itself but which will also be com-
patible with a wide range of the above-described adhesive polymer bases.
SUMMARY OF THE INVENTION
We have now found that sucrose benzoate is compatible with and provides adequate tackifying properties to a wide
range of biodegradable and/or water sensitive polymers. Thus, the present invention is directed to improved hot melt
adhesive compositions comprising a water sensitive or biodegradeable thermoplastic adhesive polymer, and a tackif ier,
optionally additionally containing a compatible plasticizer, wax and/or stabilizer; the improvement which comprises
using sucrose benzoate as the tackif ier. ! — —
More specifically, the present invention is directed to water sensitive and/or biodegradable hot melt adhesive com-
positions comprising 10 to 90% by weight of a biodegradable or water sensitive thermoplastic polymer, 5 to 80% by
weight sucrose benzoate, 0 to 80% by weight plasticizing diluent, 0 to 50% by weight wax and 0 to 3% by weight anti-
oxidant.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Suitable water sensitive and/or biodegradable thermoplastic polymers for use as the base polymer in the hot melt
adhesive compositions include, for example, hydroxybutyrate/hydroxyvalerate polymers, polylactide homo- or copoly-
mers, hydroxypropyl cellulose, hydroxy functional or a liphatic polyester s, starch esters or cellulose esters having a
degree of substitution (DS) less than 2.5 and the like. — —
Useful polymers therefore include homo- or copolymer of polylactide containing at least 20 molar percent of the lac-
tide comonomer. The general structure of the polylactide is shown below:
suitable polymers for use herein have a number average molecular weight (M,,) within the range of 10,000 to 200,000.
EP0 741 177 A2
10
15
While poly(D,L-lactide) and the meso- a re essentially amorphous, poly(L-lactid e) or poly(D-lactide) are crystalline
in nature and h^a'CTystellinenTelting point of 186"C depending on moieculaFwfeight and stereopurity. The polymers
may be prepared by ring-opening polymerization of the bimolecular cyclic ester of lactic acid with acid or base catalysts
such as PbO, SnCI 2 , SnCI 4 , ZnCI 2 . SbF 5( Sb^. or triethylamine using solution, precipitation or melt processes. Alter-
natively, they may be obtained commercially from Henley Chemicals, Inc. under the Resomere tradename; from poly
Sciences Inc. or from Ecological Chemical Products Company (Ecochem). - - — N -
In addition to homopolymers of poly(l-lactide). p^OUicWey, and pdy(meso-lactae) suitable polymers for use
herein may also be prepared by copolymerizationwifii other lactones suarsTgfySside or caprolactone. Thus,
poly(D,L-iatftf e-co-glycoside) polymers containing equimolar amounts of the lactide and glycoside components are
available from Henley Chemicals as Resomer RG502. 503, 504, 505 and 506 and are suitable for use herein. In addi-
tion, poly(D.L-iactide-co-glycoside) polymers known as Resomer RG752, 755 and 756 containing 75% of the lactide
component as well as the Resomer 858 polymer which contains 85% lactide are also suitable.
The use of this class of polymer in hot melt adhesives is described in U.S. Patent Nos. 5,252,646 and 5,312,850 to
lovine et al.
Also useful herein are the linear polyesters of 3-hydroxybutyric (HB) and 3-hydroxyvaleric (HV) acids produced
from the fermentation of sugars by the bacterium Alcaligenes eutrophus. The general structure is shown below:
20
25
CH 3
o hih
^CHf V,
O CH,
Jl
X
30
35
HYDROXYVALERATE (HV)
HYDROXYBUTYRATE (HB)
Polymers suitable for use herein contain 9 to 35% of the hydroxyvalerate component and are available from Zeneca
under the Biopol tradename.
The use of these polymers in hot melt adhesive is described in U.S. Patent No. 5,169,889 to Brady et al.
Also useful are the thermoplastic methylol polyesters containing repeating units of the formula:
40
O O CHiOK
45
50
55
wherein each of R 1 and R 2 is individually a divalent organic moiety which is predominantly hydrocarbon, each R 3 is indi-
vidually hydrogen or lower alkyl, y is a fraction from 0 to 0.5 and x is a fraction from about 0.05 to about 0.4.
These hydroxy functional polyesters are suitably prepared by contacting one or more diglycidyl ethers or diglycidyl
esters with one or more diacids or anhydrides under conditions including the use of an onium catalyst sufficient to cause
the acid moieties to react with epoxy moieties to form a polymer backbone having ester linkages and pendant methylol
moi eties. Depending upon the particular starting materials, the resulting polymer will be crystalline, semi-crystalline or
imor^housjn nature.
iepreparation of these materials are described in greater detail in US. Patent No. 5.1 71 ,820 to Mang et al. while
their use in hot melt adhesives is described in co-pending application Serial No. 08/433.578, filed on May 3, 1995 here-
with.
Aliphatic polyesters are derived from aliphatic diacids and diols. These also vary in cr ystallintty from amorphousto
highly crystalline. They are available from HOIs under the Dynapol tradename. ~
The use of hydraxypropyl cellulose in hydrophilic hot melt adhesives has been disclosed, for example, inUS. Pat-
ent 5,356,963 issued October 18, 1994. Similarly, cellulose or starch esters, especially cellulose acetate and starch
EP0 741 177 A2
acetatejiavinga degree of substitution less than 2.5 may also be tackified with sucrose benzoate in accordance with
^^^rnb^M^ *"* eSterS 1101 melt h3S b6en diSC,0Sed in ' amo "9 U S. 5.360.845
Depending on the base polymer, various grades of sucrose benzoate may be employed as the tackrfier For our-
posesherem we have found.that the alcohol soluble partially esterified grade of sucrose benzoate is the most generally
compatible. This grade is a light colored, clear noncrystalline s olid with a softenin g poirrtoLabout 95'C For some base
polymers, it is also possible to use the non-alcotoTol^ic^oTuble grade whi* is substertW^ esterified and is
water-dear non^c^y^ ^ noted ^ grade j s ^
Ln E^??" ^/T beCaUS t! ^ Unre8Cted ****** Srades are available commerciaiiy
Lmk from Velacol Chemical Corporation. The amount of sucrose benzoate required will depend upon the other components
in the adhesive as well as upon the desired end properties; however, it is usually present in an amount of 5 to 80% bv
weight, preferably 20 to 60% by weight. "moum or o to eu% Dy
/und2!l! ^ t P ST ntS r ; C0 I 1Venti0nally UtHi2ed in h0t m6lt adhesive ""PWltkw may also be used herein. It will be
f understood that the particular components used will vary depending upon the intended end use of the adhesive as well
V 75 Ca T UH l.i *• ?»» " Bh *• *e™P«a«ic polymer errployed. ft wiH a'.so be r^TZZ rr^
t water sensitive or biodegradable the additive used, the more degradable will be the resultant adhesive
«J22 ( 2!r ^ 8 ^ JPP |iC8tion - 80(1 Particularly for uses requiring pressure sensitive properties, various
ZSSSES^Z ? °5 ^ 8180 be "T in *• J"*™? plastidze*
1 , " cl " de P*" 8 ' 8 * 8 Plashcaers such as dioctyl phthalate: l.^ujd polyesters such as3^aco^0> om Huls benzoate
*-LS2^h ,U * d S hy,e ?K 9 ' y< ?' dib6nZOate (- *' ^^SO-available comme ^ally tJ^&fsSSSS-
S ^£T£ m °' e ,raCti ° n 01 which have been esterified ranges from 0.5 to 0 95
fS Be ^r^S° h Hydr0Xy from Veteico1 ) : P^^ 8 P" 88 ^ such as t-butylphenyl diphenyl phosphate (If
n^S SSSTTS? * o° m M0nSant ° ): P"***™ and^tives thereof suc^stephe^
nyl ether of ^(ethylene glycol) (e.g.. Pycal 94 available commercially from ICI) as well as liquid rosin derivatives haT-
2s ,ng Ring and Ball melting points be«Wc such as the methyl ester oi hydrogenat« «EJ5 TSSTd
EiJEES ? h ^ 5 V69etaWe 8nd animal * Such 88 esters of fat^aSs and polymerization pTTc£
hereof. If used, the plasterer is generally present in amounts up to about 80% by weight, preferably 10-to 40%^
™ ™ ^ apjirations conventionally employing adhesives based on these water sensitive or btodegrada^lymers
so wjrwMrt the use of wax diluents in order to reduce the melt viscosity or cohesive characteristics offteCTeTt
adhesive composrtions wrthout appreciably decreasing their adhesive bonding characteristics Thesfwaxe "are often
T^r" £** T T M P ~* pr °P ertes - ■ P«St the waxes Se^Sina^ J to
about 50% by weight, preferably 5 to 35% by weight. ^
Suitable waxes include N-(2-hydroxyethv0-12-hydroxy stearamide wax. hydrogenated castor oil. oxidized synthetic
35 waxes, polyethylene oxide) having a weight average molecular weight above about 1000 ano^nctiSSSd Shetic
waxes such as carbonyl containing Escomer H101 from Exxon Tunci.onai.zed synthetic
conlS^^r^ ** "*T" formulations describ «J "erein may contain both wax and plasticizer
components so that the presence of one or the other is not mutually exclusive
riho ^r n L the a " >liCable s * abilizere w antioxidants which may be included herein are high molecular weight hindered
40 phenote and mutWu.Kt.onal phenols such as sulfur and phosphorous-containing phenols. Representee h nde ed
r^^^ ^^oP-onate; n-octadecyl 3.5<li-tert*utyl^hydroxyphenyl) propionate; 4.4'-methy lenebis
^h^lr?? 8 " 0 ^ 4,4 '"^ 8 ^-^-o-cresol); 2.Mi-tert-burytohVnd; 6-(4*y*^^
^t 88 may 68 incorporated into the hot melt compositions in order to modify certain properties thereof
Among these additives may be included colorants such as titanium dioxide; and fillers such as talc and day rtc ThSe
may also be present .n the adhesive small amounts (e.g., less than about 20% by weight and prefe^lv S to 20% £
50 S?fiS ih t the r P,aStiC and/ ° r P ° ,ymere 68 are conventiona'y^S,^ SSS - iSSS?
impart flex* lity. toughness, strength andtor water sensHivity. Suitable thermoplastic polymers include ethylene tJnS
acetate, ethylene acryiic acid, ethylene methyl acrylate and ethylene n-butyl aaylate ccXm^s cor^n^P to S
viny. or acrytete monomers. Suitable hydrophilic polymers inc.Se polyv^alcohThy^Z ^SSXSSSS
pyl cejulose. polyvinyl methyl ether, polyethylene oxide). polyvinyipSone and the Z hydroxypro-
n.rJ^l I™* adh8SiVe COmp ° Sitions be fo^uteted using techniques known in the art. An exemplary proce-
ISSF ^ aan9 ! PP ™ C,mately 40%ofthetotel *ackJfying resin concentration with all the polymer^ mSSL
S 8 range of from up to about 1 90-C. After the resin has mSed 'the^Sure fe
lowered to 150 to 165'C. M.x.ng and heating are continued until a smooth, homogeneous mass is obtained whereupon
EP0741 177A2
the remainder of the tackifying resin is thoroughly and uniformly admixed therewith. The adhesives disclosed her in
may be employed in a wide variety of uses as are known in the art The adhesives described herein may be effectively
utilized in a variety of packaging and carton sealing applications. The non-pressure sensitive adhesives may also be
used to bind a plurality of sheets in a wide range of bookbinding operations. They may also be used for laminating tissue
5 and/or screen-reinforced tissue layers such as are used in individual or roll use applications as in wTpersrpaper towels r
toilet tissue and other consumer or industrial end uses. When formul ated with plasticizer s, the resultant adhesives may
be used in the assembly or construction of various disposable articles including, but not limited to sanitar y napkins, dis-
posable diapers, hos pital gowns, bed pad s a nd the like. In particular, adhesives are useful for the assembly of dispos-
able articles using spray orTnulPine construction techniques wherein at least one flexible film substrate is bonded to
10 at least one tissue, non- woven, polyolefin or other flexible polymeric film substrate. In addition, the adhesives may be
useful in the bonding ofelastc to polyethylene, polypropylene or non-woven substrate so as, for example, to impart
elongation resistant gathers thereto. The adhesive may also be utilized in less demanding disposable construction
applications such as for end or perimeter seating.
In the following illustrative examples all parts are given by weight and all temperatures in degrees Celsius unless
is otherwise noted.
EXAMPLE I
This example shows the preparation of a hot melt adhesive with completely biodegradable components. Here the
20 base polymer is polylactide, which can be formulated with either the regular or ASG grade of sucrose benzoate.
A
B
Polylactide
30
30
Sucrose Benzoate (ASG)
40
Sucrose Benzoate Regular
40
Crtrof lex 2
30
30
Irganox 1010
0.5
0.5
Crtrof lex 2: Triethyt citrate from Morf lex Irganox
1010 is a hindered phenol antioxidant
35 The above examples are clear, pressure sensitive with excellent mechanical properties.
EXAMPLE II
This shows how another biodegradable hot mett adhesive can be made based on hydroxybutyrate/valerate
40 (PHV/B), with other biodegradable components. PHV/B is available from Zeneca under the tradename Biopol.
C
Biopol
40
Sucrose Benzoate (ASG)
40
Surfbnic DNP-100
20
Irganox 1010
0.5
Surfonic DNP 100 Dinonyl phenol
10 mole ethylene oxide from
Huntsmen
Example C is an opaque non-pressure sensitive hot mett with good compatibility.
55
EXAMPLE HI
This experiment shows how hydroxypropyi cellulose, Klucel, available from Aqualon in varying molecular weight
ranges can be made into a water sensitive/dispersabie hot melt adhesive with the alcohol soluble grade of sucrose ben-
i
EP0 741 177 A2
zoate as the tackHier.
D
KlucelL
15
Sucrose Benzoate (ASG)
50
Pycal94
20
Heroolyn D
15
Irganox 1010
0.5
Pycal 94 is an ethoxylated phenol with
approximately 4 moles of ethyleneox-
ide, available from 1CI Specialty Chem-
icals.
Hercolyn D is the methyl ester of rosin,
available from Hercules.
20 The above example adhesive was clear, water sensitive, with excellent mechanical properties and stability.
Other grades of Wucel, varying in molecular weight as follows may also be used:
Type
MW*
H
1,150,000
M
850,000
G
370,000
J
140.000
L
95,000
E
80,000
'Weight average
molecular weight
35 determined by size
exclusion chromato-
graph.
The preferred grades for use herein are E, L and J.
40
EXAMPLE IV
This shows how a water sensitive and biodegradable polymer, starch acetate can be made into a hot melt adhesive
with the alcohol soluble grade of sucrose benzoate. In this sample, the viscosity was measured using a BrooWield vis*
45 cometer (Spindle 27) at various temperatures as noted.
so
55
EP0 741 177 A2
E
Starch Acetate, DS = 1.6*
45
Macol 206EM
45
Sucrose Benzoate (ASG)
10
Sarttovar A
0.5
TNPP
0.5
Viscosity (cp)
250°F
5,238
275°F
2.670 1
300°F
1.635
325°F
1,195
350°F
845
Macol 206EM 6 mote ethoxylate of
Bisphenol A from PPG
Santovar A is a hindered phenol available
from Monsanto
* D.S. - degree of substitution per glucose
repeat unit, with 3 being full acetylation
EXAMPLE V
In the following exarrple various grades of methylol poly(ether, esters) available from Dew Chemical were evalu-
ated with the alcohol soluble grade of sucrose benzoate. In preparing the following samples, a heavy duty mixer which
had been heated to 165°C and which was equipped with a stirring paddle was charged with 40% of the tackifying resin
and/or diluent. After melting of the resins, stirring was then initiated whereupon the polyester was added slowly at
165°C over a one-half hour period after which the temperature was lowered to 150°C. Heating and stirring were contin-
ued until a homogeneous mass was obtained whereupon the remainder of the tacWfying resin and/or diluent was
admixed therewith.
The samples were tested using the following procedures:
Viscosity measurements were determined after 30 minutes using a Brookfield viscometer (Spindle 27) at 250°E
The adhesive was also subjected to Peel/Shear testing such as is conventionally required in the packaging industry.
Peel Temperature Test: A bead of test adhesive approximately 1/8 inch in diameter is applied at 325°F to 350°F with a
glass rod onto 60 pound/ream kraft paper. A second sheet of the same paper is superimposed on the first sheet within
2 seconds and pressed thereto to form a kraft-to-kraft bond. The bonded sheets are then cut perpendicular to the adhe-
sive line into 1 inch wide strips. Duplicate bonded specimens are placed in an oven with one free end of the specimen
attached to a fixed support and a 100 gram load suspended from the other sheet at the same end of the bond. The oven
temperature is then increased in 10°F increments at 15 minute intervals. The temperature at which bond delamination
occurred is specified as the peel temperature.
Shear Temperature Test: Samples are prepared as in peel temperature test but separate sheets of Kraft at opposite
ends of the bonded specimen are suspended and weighted to stress the bond in a shear mode. The temperature of the
oven is increased as in peel test until failure occurs.
Adhesion Test: A molten bead of hot melt at 325°F to 350°F was drawn across the middle (widthwise) of a r x 3"
strip of corrugated paper. A second strip of corrugated paper was then immediately superimposed upon the first and a
50 gram weight placed on top of the construction. The kraft-to-kraft bonds were then aged 24 hours at room tempera-
ture. After aging, the samples were stressed by hand at the temperature noted (0°F t 20°F or 40°F) in a 90° peel mode.
The presence of f ber tear indicates excellent adhesion.
Tack and Range were measured by drawing out a 3 mil thick adhesive film and qualitatively measuring the tack by
determining how many successive finger prints could be made in the film before it set The range or open time indicates
the number of seconds during which the finger prints can be made. Cigarette plug adhesion was measured by applying
EP0741 177 A2
a bead of adhesive to cigarette plug paper, forming a bond and conditioning the bond for 24 hours at room temperature.
After conditioning, the bonds were pulled at 180° mode by hand.
Some of the adhesives were also tested for t hermal stab ility by storing at 275°F for 24 hours and then noting the
appearance of the adhesive. v -^=~^ — -
""" ^"Samples J and K are typical formulations used in non-pressure sensitive packaging case and carton seal type
application. In these samples, the crystalline poly(ether t ester) formed from the reaction of hydroquinone diglyctdyl
ether with 1 , 1 O-decandicarboxyiic acid was employed (CRY). These formulations have low viscosity and good high tem-
perature performance as can be seen from the good peel/shear values. Also, the products have good lo w temper ature
performance as is demonstrated by the good adhesion to corrugated at low temperatures. Lastly, these products"fiave
excellent adhesion to cigarette plug wrap.
F
G
CRY
50
50
Sucrose Benzoate ASG
20
Benzoflex 2-45 High Hydroxyl
30
10
Paracin 220
20
20
Irganox 1010
0.5
0.5
Viscosity (cp) @ 250°F
5,612
10,920
Peel (F)
100
110
Shear (F)
180
180
Tack
Slightly Aggressive
Aggressive
Range
3 seconds
4 seconds
Corrugated Adhesion
0°F
50%
80%
20°F
70%
85%
40°F
70%
85%
Cigarette Plug Wrap Adhesion
Excellent
Excellent
Benzoflex 2-45 High Hydroxyl - diethylene glycol benzoate where about 0.75 mole
fraction of hydroxyl groups have been esterified to benzoate esters from Velsicol
Chemical Corporation.
The test results presented above show the adhesives to be particularly suitable for packaging applications such as
case and carton sealing due to its low viscosity, good ffoer tear and acceptable peel and shear values.
Another series of hot melt adhesives were formulated into pressure sensitive formulations using an essentially
amorphous poly(ether, ester) derived from the reaction of bisphenol A diglyckJyl ether and 1 ,4-cydohexanedicarboxylic
acid~(AMP)7"' -
EP0741 177 A2
The compositions and test results are shown in the tables which follow:
H
AMP
25
Sucrose Benzoate ASG
40
Benzof lex 2-45 High Hydroxyl
35
Irganox 1010
0.5
Comments
Good compatibility
Viscosity (cp)
@ 275°F
4115
@300°F
2250
The resultant adhesive was evaluated and found to give a clear water white product. Poly/non-woven bonds were
20 made by heating the adhesive to approximate ly^! 35° C and apply ing a thin-bead of adhesive onto the polyethylene and
quickly mating the non-woven and next applying compression with a 200~g*"weight or rolling over the bond with a 5 lb.
roller. The bonds were then pulled by hand and gave deformation of the substrate which indicated good penetration and
good adhesion properties.
In the following formulations several waxes were used in the adhesive formulations in conjunction with the
25 poly( ether, ester) and the sucrose benzoate.
55
EP0 741 177 A2
1
i
i
j
t
L
5
AMP.
on
on
on
on
OUCrOSG DGnZOole
An
Aft
An
An
Castor wax
lu
rvemamiue w-*hj
lO
in
raracin 2^u
10
D JT_JJ1_ JlUjlU
benzotiex ou
or
oenzoriex 2-45 mgn nyaroxyi
on
30
oc
25
do
15
irganox ioio
n c
0.5
n c
0.5
U.O
n r
comments
compatible
compatible
uompduuie
compatiuie
viscosity (cp)
© 250 r
2,455
not testeo
20
<§> 275 r
1,340
^ inn
4,100
1,290
(g> 300 r
TOE
735
1,420
715
uorrugateo Aanesion
25
ADC
Or
* ac/
10%
not testeo
ncv
U%
0%
20 r
20%
0
0
40° F
ACQ/
95%
4 a
10
10
Peel (°F)
4 AA
100
•* OA
130
140
30
Shear <°F)
100
170
170
Tack
Aggressive
Very Aggressive
Very Aggressive
Very Aggressive
Range (seconds)
8
1
5
2
35
Castor Wax, Cas Chem: Hydrogenated castor oil
Kemamide W40, Witco: N.N'-ethyienebisstearamide
40 As the results indicate, all of the waxes evaluated were compatible in the formulations. In Samples I, J, K and L the
low temperature performance was not within acceptable levels; however, the high temperature performance was within
acceptable levels suitable for pressure sensitive type applications, such as in the construction of disposable articles
where low temperature performance is not critical.
45 Claims
1 . A hot melt adhesive composition comprising 10 to 90% by weight of a biodegradable thermoplastic adhesive poly-
mer selected from the group consisting of hydroxybutyrate/hydroxyvalerate polymers, poiylactide homo- or copoly-
mers, hydroxypropyl cellulose, cellulose or starch esters having a degree of substitution less than 2.5, hydroxy
so functional or aliphatic polyesters; 5 to 80% by weight sucrose benzoate, 0 to 80% by weight of a plasticizing diluent
selected from the group consisting of phthalate plasticizers, liquid plasticizers, benzoate plasticizers, phosphate
plastidzers, poly(ethyiene glycols) and derivatives thereof; liquid rosin derivatives having Ring and Ball melting
points below about 60«C, vegetable and animal oils and the polymerization products thereof; 0 to 50% by weight of
a wax selected from the group consisting of N-(2-hydroxy -ethyl)* 12 -hydroxy stearamide, hydrogenated castor oil,
55 oxidized synthetic waxes, polyethylene oxide) having a weight average molecular weight above about 1000 and
functionalized synthetic waxes, and 0 to 3% by weight antioxidant
2. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is a homo- or copolymer of
poiylactide containing at least 20 molar percent of the lactide comonomer.
EP 0 741 177 A2
3. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is a linear polyester of 3-
hydroxybutyric and 3-hydroxyvaleric acid.
4. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is a thermoplastic methylol
5 polyester prepared by the reaction of one or more diglyckJyl ethers or diglycidyl esters with one or more diacids or
anhydrides.
5. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is hydroxypropyl cellulose.
w 6. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is starch acetate having a
degree of substitution less than 2.5.
7. The hot melt adhesive of Claim 1 wherein the water sensitive or biodegradable polymer is an aliphatic polyester.
is 8. The hot melt adhesive of Claim 1 wherein the sucrose benzoate is present in an amount of 1 0 to 40% by weight.
9. The hot melt adhesive of Claim 1 wherein the sucrose benzoate is partially esterif ied.
20
25
30
35
40
45
50
55
(19)
(12)
Europfiisches Patentamt
European Patent Office
Office europeen ties brevets (11) EP 0 741 177 A3
EUROPEAN PATENT APPLICATION
(88)
Date of publication A3:
(51) Int. Cl. 6 : C09J 11/06
19.03.1997 Bulletin 1997/12
(43)
Date of publication A2:
06.11.1996 Bulletin 1996/45
(21)
Application number: 96105289.1
(22)
Date of filing: 02.04.1996
(84)
Designated Contracting States:
(72) Inventors:
BE DE FR GB IT LU NL SE
• Sharak, Matthew L
Franklin Park, New Jersey 08823 (US)
(30)
Priority: 03.05.1995 US 433285
• Paul, Charles W.
(71)
Applicant: National Starch and Chemical
Madison, New Jersey 07940 (US)
Investment
(74) Representative: Hagemann, Helnrich, Dr.rer.nat,
Holding Corporation
Dipl.-Chem. et at
Wilmington, Delaware 19809 (US)
Patentanwdtte
Hagemann & Kehl
Postfach 86 03 29
81630 MOnchen (DE)
(54) Sucrose Benzoate as a tackHier for water sensitive or biodegradable hot melt adhesives
(57) Hot melt adhesive compositions are prepared
from a water sensitive or biodegradeable thermoplastic
adhesive polymer using sucrose benzoate as a tackif ier.
More particularly, hot melt adhesive compositions are
prepared from 10 to 90% by weight of a biodegradable
or water sensitive thermoplastic polymer, 5 to 80% by
weight sucrose benzoate, 0 to 80% by weight plasticiz-
ing diluent, 0 to 50% by weight wax and 0 to 3% by
weight antioxidant.
EP0 741 177 A3
European Patent
Office
EUROPEAN SEARCH REPORT
Application Noatber
EP 96 1G 5289
DOCUMENTS CONSIDERED TO BE RELEVANT
Category
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CLASSIFICATION OF THE
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